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Holiday Rentals in Kissimmee, Florida

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All 4,227 Rentals in Kissimmee
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From
$296
Per Night
7 Bedrooms, 6 Bathrooms, Sleeps 16
Wheelchair access, Private Pool, Private pool & more
15 photos Details
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From
$246
Per Night
3 Bedrooms, 3 Bathrooms, Sleeps 12
Pet friendly, Water Views, Elder access & more
9 photos Details
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From
$291
Per Night
7 Bedrooms, 4 Bathrooms, Sleeps 14
Suitable for children, Elder access, Parking & more
14 photos Details
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Also consider
Elegant Townhome in a quiet gated community
3 Bedrooms, sleeps 6
$70 / night
Orlando home rental-4 bed/3 "gorgeous" pool/spa
4 Bedrooms, sleeps 8
$128 - $192 / night
Big Brand New 4 Duplex  Home with free Wi-Fi
4 Bedrooms, sleeps 9
$128 - $182 / night
Luxury villa on lake * Vacation for under $500 PW*
3 Bedrooms, sleeps 8
$73 - $76 / night
From
$245
Per Night
5 Bedrooms, 5 Bathrooms, Sleeps 12
Internet, Air Conditioning, Suitable for children & more
20 photos Details
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From
$1,058
Per Week
4 Bedrooms, 3 Bathrooms, Sleeps 10
Private Outdoor Pool (Unheated), Private pool & more
13 photos Details
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From
$338
Per Night
6 Bedrooms, 5 Bathrooms, Sleeps 16
Suitable for children
20 photos Details
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From
$162
Per Night
4 Bedrooms, 3 Bathrooms, Sleeps 9
Suitable for children, Elder access
15 photos Details
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From
$183
Per Night
6 Bedrooms, 4 Bathrooms, Sleeps 13
Booking
Washer/Dryer, Air Conditioning & more
22 photos Details
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From
$116
Per Night
4 Bedrooms, 3 Bathrooms, Sleeps 8
Water Views, Air Conditioning, Internet & more
12 photos Details
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From
$188
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 4
Internet, Other outdoor space, Air Conditioning & more
33 photos Details
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From
$47
Per Night
1 Bedroom, 1 Bathroom, Sleeps 4
Booking
Pool, Suitable for children, Parking & more
5 photos Details
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From
$148
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 8
Air Conditioning, Garden, Wi-Fi & more
18 photos Details
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From
$118
Per Night
4 Bedrooms, 3 Bathrooms, Sleeps 8
Suitable for children
14 photos Details
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From
$111
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 6
Internet, Elder access, Suitable for children
12 photos Details
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From
$135
Per Night
4 Bedrooms, 3 Bathrooms, Sleeps 8
Air Conditioning, Pool, Public pool
40 photos Details
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From
$262
Per Night
6 Bedrooms, 5 Bathrooms, Sleeps 12
Other outdoor space, Sauna, Internet
21 photos Details
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From
$365
Per Night
4 Bedrooms, 3 Bathrooms, Sleeps 10
Parking, Hot Tub, Private pool & more
13 photos Details
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From
$118
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 6
Suitable for children, Other outdoor space & more
17 photos Details
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From
$113
Per Night
4 Bedrooms, 3 Bathrooms, Sleeps 8
Internet, Private pool, Air Conditioning & more
10 photos Details
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From
$63
Per Night
1 Bedroom, 1 Bathroom, Sleeps 6
Fitness Room, Pool, Internet & more
9 photos Details
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From
$146
Per Night
5 Bedrooms, 3 Bathrooms, Sleeps 10
Public pool, Pool, Heated Pool & more
23 photos Details
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From
$113
Per Night
4 Bedrooms, 2 Bathrooms, Sleeps 8
Bookings
Parking, Housekeeping Optional & more
24 photos Details
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From
$433
Per Night
6 Bedrooms, 4 Bathrooms, Sleeps 14
Hot Tub, Private pool, Elder access & more
19 photos Details
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From
$113
Per Night
3 Bedrooms, 3 Bathrooms, Sleeps 6
Sauna, Private pool, Grill & more
29 photos Details
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From
$124
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 6
Other outdoor space, Internet, Air Conditioning
21 photos Details
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From
$117
Per Night
3 Bedrooms, 3 Bathrooms, Sleeps 6
Internet, Parking, Child pool & more
26 photos Details
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From
$91
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
Other outdoor space, Children's Pool & more
33 photos Details
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From
$176
Per Night
6 Bedrooms, 6 Bathrooms, Sleeps 14
Grill, Internet, Air Conditioning & more
19 photos Details
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From
$149
Per Night
5 Bedrooms, 2 Bathrooms, Sleeps 10
Pet friendly, Hot Tub, Other outdoor space & more
9 photos Details
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From
$114
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 8
Wi-Fi, Shared Outdoor Pool (Heated) & more
24 photos Details
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From
$117
Per Night
3 Bedrooms, 3 Bathrooms, Sleeps 8
Air Conditioning
12 photos Details
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From
$154
Per Night
7 Bedrooms, 5 Bathrooms, Sleeps 16
Private pool, Air Conditioning, Grill & more
16 photos Details
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From
$172
Per Night
5 Bedrooms, 3 Bathrooms, Sleeps 12
Bookings
Water Views, Elder access, Suitable for children & more
33 photos Details
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From
$161
Per Night
5 Bedrooms, 3 Bathrooms, Sleeps 10
Suitable for children, Shared Tennis Court & more
30 photos Details
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From
$117
Per Night
3 Bedrooms, 3 Bathrooms, Sleeps 8
Hot Tub, Suitable for children, Elder access & more
35 photos Details
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From
$117
Per Night
4 Bedrooms, 2 Bathrooms, Sleeps 8
Pool, Public pool, Internet & more
20 photos Details
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From
$188
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 6
Washer/Dryer, Suitable for children, Parking & more
14 photos Details
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From
$149
Per Night
5 Bedrooms, 3 Bathrooms, Sleeps 10
Private pool, Waterfront, Internet & more
15 photos Details
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From
$117
Per Night
3 Bedrooms, 3 Bathrooms, Sleeps 8
Elder access, Garden, Parking & more
35 photos Details
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From
$203
Per Night
5 Bedrooms, 3 Bathrooms, Sleeps 12
Air Conditioning, Internet
15 photos Details
Make Enquiry
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Book Online(2689)
Use filters to find the best results!

Suitability

  • Wheelchair access (605)
  • Elder access (1,723)
  • Suitable for children (2,418)
  • Pet friendly (197)
  • Smoking allowed (89)

Amenities

  • Internet (2,943)
  • Air Conditioning (2,890)
  • All pools (2,621)
  • Other outdoor space (1,957)
  • Washer/Dryer (1,771)
  • View all amenities
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